18085-02-4

Basic information

• Product Name: 3,4-DIACETOXY-1-BUTENE
• Synonyms: 3,4-DIACETOXY-1-BUTENE;3-BUTENE-1,2-DIOL DIACETATE;DACB;3,4-DIACETOXY-1-BUTENE, 99.5+%;Vinylglycoldiacetate;3,4-DIACETOXY-1-BUTENE 97%;1,2-diacetoxybut-3-ene;3-Butene-1,2-diol diacetate, DAcB
• CAS NO: 18085-02-4
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• EINECS: 421-720-5
• Product Categories: Intermediates;Miscellaneous Reagents
• Mol File: 18085-02-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 95-96 °C10 mm Hg(lit.)
• Flash Point: 196 °F
• Appearance: /
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.182mmHg at 25°C
• Refractive Index: n20/D 1.43(lit.)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 5.1[at 20 ℃]
• Water Solubility: 26.2g/L at 25℃
• CAS DataBase Reference: 3,4-DIACETOXY-1-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIACETOXY-1-BUTENE(18085-02-4)
• EPA Substance Registry System: 3,4-DIACETOXY-1-BUTENE(18085-02-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 1
• Hazardous Substances Data: 18085-02-4(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO YELLOWISH LIQUID

Uses

Different sources of media describe the Uses of 18085-02-4 differently. You can refer to the following data:
1. Intermediate in the preparation of 1,4-Butanediol and tetrahydrofuran.
2. Diacetoxybutene is used in method for isomerization of allyl compounds using gold or platinum catalyst. An intermediate in the preparation of 1,4-Butanediol and tetrahydrofuran.

General Description

3,4-Diacetoxy-1-butene (3,4-DAB) is a diacetoxybutene derivative. 1,3-butadiene undergoes oxidative acetoxylation in the presence of palladium-based IMCs (intermetallic compounds) to form 3,4-DAB as one of the product.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H12O4/c1-4-8(12-7(3)10)5-11-6(2)9/h4,8H,1,5H2,2-3H3/t8-/m1/s1

Upstream product

• 1576-98-3 1,4-diacetoxybut-2-ene 
• 64-19-7 acetic acid 
• 106-99-0 buta-1,3-diene 
• 189162-38-7 acetoxybut-2-enyl trichloroacetimidate 
• 25260-60-0 cis-1,4-bis(acetyloxy)but-2-ene 
• 1576-98-3 trans-1,4-diacetoxy-2-butene 
• 31469-25-7 1,1-bis(trimethylsiloxy)-2-methylprop-1-ene 
• 821-06-7 (E)-1,4-dibromobutene 
• 127-09-3 sodium acetate 
• 930-22-3 epoxybutene 
• 108-24-7 acetic anhydride 
• 2570-63-0 thallium(III) triacetate 
• 497-06-3 3,4-butenediol 
• 75-36-5 acetyl chloride 

Downstream Products

• 1257322-07-8 dimethyl-1-(4-methylphenylsulfonyl)-3-vinyl-2,3-dihydroquinoline-4,4(1H)-dicarboxylate 
• 1182278-44-9 (E)-4-(4-iodophenyl)but-3-ene-1,2-diyl diacetate 
• 1182278-46-1 (E)-4-(3-nitrophenyl)but-3-ene-1,2-diyl diacetate 
• 1182278-47-2 (E)-4-(2-methoxyphenyl)but-3-ene-1,2-diyl diacetate 
• 1151782-08-9 (E)-4-(4-bromophenyl)but-3-ene-1,2-diyl diacetate 
• 1151782-09-0 (E)-4-(4-fluorophenyl)but-3-ene-1,2-diyl diacetate 
• 1182278-38-1 (E)-4-p-tolylbut-3-ene-1,2-diyl diacetate 
• 119420-99-4 (E)-4-phenylbut-3-ene-1,2-diyl diacetate 
• 1182278-37-0 (E)-4-(4-methoxyphenyl)but-3-ene-1,2-diyl diacetate 
• 1182278-41-6 (E)-4-(4-chlorophenyl)but-3-ene-1,2-diyl diacetate 
• 7553-56-2 iodine 
• 16939-73-4 (E)-2-heptenyl acetate 
• 83540-70-9 (Z)-2-Hepten-1-yl acetate 
• 89543-93-1 Acetic acid 2-acetoxy-1-(3-phenyl-4,5-dihydro-isoxazol-5-yl)-ethyl ester 

Relevant articles and documents

Process for preparation of 4-acetoxy-2-methyl-2-butene-1-aldehyde and intermediates thereof

The invention relates to the technical field of organic synthesis, and discloses a method for preparing 4-acetoxy-2-methyl-2-butene-1-aldehyde and an intermediate thereof. The method comprises the following steps: (1) in the presence of an esterification reagent, carrying out esterification reaction on 1, 4-butenediol to obtain 1, 4-butenediol diacetate; (2) in the optional presence of a first catalyst, carrying out an isomerization reaction on the 1, 4-butenediol diacetate to obtain 3, 4-diacetoxy-1-butene; (3) in the presence of a phosphorus-containing ligand and a rhodium catalyst and/or a cobalt catalyst, carrying out hydroformylation reaction on the 3, 4-diacetoxy-1-butene, carbon monoxide and hydrogen to obtain 2-methyl-3, 4-diacetoxy-1-butyraldehyde; (4) in the optional presence of a third catalyst, carrying out an elimination reaction on the 2-methyl-3, 4-diacetoxyl-1-butyraldehyde to obtain the 4-acetoxyl-2-methyl-2-butene-1-aldehyde. The method provided by the invention has the advantages of mild reaction conditions, environmental friendliness and high yield.

METHOD FOR ISOMERIZING ALLYL COMPOUND

Catalyst for isomerization of allyl compound in method, catalyst by restraining degradation caused, low catalyst levels usage in high yield isomer make it possible to obtain a an industrially advantageous method provides for isomerization of allyl compounds. In the presence of catalyst, raw material allyl compound corresponding allyl compound as isomerizing method, before isomerization using catalyst raw material allyl compounds organic phosphorus compound-containing solution is characterized by contacting the isomerization method.

Catalytic asymmetric synthesis of chiral allylic esters

A broadly useful catalytic enantioselective synthesis of branched allylic esters from prochiral (Z)-2-alkene-1-ols has been developed. The starting allylic alcohol is converted to its trichloroacetimidate intermediate by reaction with trichloroacetonitrile, either in situ or in a separate step, and this intermediate undergoes clean enantioselective SN2′ substitution with a variety of carboxylic acids in the presence of the palladium(II) catalyst (Rp,S)-di-μ-acetatobis[(η5- 2-(2′-(4′-methylethyl)oxazolinyl)cyclopentadienyl-1-C,3′-N) (η4-tetraphenylcyclobutadiene)cobalt]dipalladium, (R p,S)-[COP-OAc]2, or its enantiomer. The scope and limitations of this useful catalytic asymmetric allylic esterification are defined.